CN100402525C - Pyridine derivatives as fungicidal compounds - Google Patents
Pyridine derivatives as fungicidal compounds Download PDFInfo
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- CN100402525C CN100402525C CNB2004800042371A CN200480004237A CN100402525C CN 100402525 C CN100402525 C CN 100402525C CN B2004800042371 A CNB2004800042371 A CN B2004800042371A CN 200480004237 A CN200480004237 A CN 200480004237A CN 100402525 C CN100402525 C CN 100402525C
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- halogen atom
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- atom
- alkylthio
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Organic Chemistry (AREA)
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- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
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- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Compound of general formula (I) and process for preparing this compound. Novel intermediate of general formula (E): for the preparation of compound of general formula (I) Fungicidal composition comprising a compound of general formula (I). Method for treating plants by applying a compound of general formula (I) or a composition comprising it.
Description
Invention field
The present invention relates to novel N-[2-(2-pyridyl) ethyl] carboxamides derivatives, its preparation method as fungicide composition, particularly with the application of fungicide composition form, reaches the method for using these compounds or its composition for preventing and controlling phytopathogenic fungi.
Background technology
International Patent Application WO 01/11965 has illustrated a class Fungicidal compounds shown in the general formula that comprises compound of the present invention.But The compounds of this invention is specifically not open in this patent application, does not test its activity as mycocide yet.
But in agriculture field, always be to use than the more activated compound of those skilled in the art compound known, purpose is the amount reduction with the active substance of peasant's use, validity is kept at least equating with known compound simultaneously.
Have been found that now having selected a compounds is derived from some new compound with above-mentioned advantage.
Therefore, the present invention relates to N-[2-(2-pyridyl) ethyl of following general formula (I)] carboxamides derivatives:
Wherein:
-X can be Sauerstoffatom or sulphur atom;
-Y can be identical or different, can be halogen atom, nitro, cyano group, hydroxyl, carboxyl, C
1-C
8-alkyl has the C of 1-5 halogen atom
1-C
6-haloalkyl, C
1-C
8-alkylamino, two-C
1-C
8-alkylamino, C
1-C
8-alkoxyl group has the C of 1-5 halogen atom
1-C
6-halogenated alkoxy, C
1-C
8-alkylthio has the C of 1-5 halogen atom
1-C
6-halogenated alkylthio, C
2-C
8-alkene oxygen base has the C of 1-5 halogen atom
2-C
8-haloalkene oxygen base, C
3-C
8-alkynyloxy group has the C of 1-5 halogen atom
3-C
8-halo alkynyloxy group, C
3-C
8-cycloalkyl, C
1-C
8-alkoxy carbonyl, C
1-C
8-alkyl sulfinyl, C
1-C
8-alkyl sulphonyl has the C of 1-5 halogen atom
1-C
8-haloalkyl sulfinyl has the C of 1-5 halogen atom
1-C
8-halogenated alkyl sulfonyl or C
1-C
6-Alkoximino-C
1-C
6-alkyl;
-R
1Can be hydrogen atom, cyano group, nitro, formyl radical, C
1-C
6-alkyl, C
1-C
6-alkyl-carbamoyl, C
2-C
6-thiazolinyl, C
2-C
6-alkynyl has the C of 1-7 halogen atom
1-C
6-haloalkyl, C
1-C
6-alkoxy-C
1-C
6-alkyl, C
1-C
6-Qing Wanji, C
1-C
6-aminoalkyl group, C
3-C
6-cycloalkyl, C
1-C
6-alkyl-carbonyl has the C of 1-5 halogen atom
1-C
6-halogenated alkyl carbonyl, C
1-C
6-alkoxy-C
1-C
6-alkyl-carbonyl, C
1-C
6-alkyl alkylthio base or the C of 1-5 halogen atom is arranged
1-C
6-haloalkyl sulfane base;
-n is 1,2,3 or 4;
The optional 5-that replaces of-Het representative, the non-fused ring heterocycle of 6-or 7-unit has 1,2 or 3 identical or different heteroatoms; Het connects by carbon atom.
In content of the present invention:
-halogen refers to fluorine, bromine, chlorine or iodine;
-heteroatoms refers to N, O or S.
According to the present invention, X represention oxygen atom or sulphur atom.Preferably, X represention oxygen atom.
According to the present invention, the 2-pyridyl can be at all sites by (Y)
nReplace, wherein Y and n are by top definition.Preferably, the present invention relates to N-[2-(2-pyridyl) ethyl of general formula (I)] carboxamides derivatives, have following different characteristics alone or in combination:
-to n, n is 1 or 2.Better n is 2.
-to Y, at least one Y substituting group is a halogen atom, C
1-C
8-alkyl has the C of 1-5 halogen atom
1-C
6-haloalkyl or C
1-C
6-alkoxy-C
1-C
6-alkyl-carbonyl.Better, at least one Y substituting group is the C that 1-5 halogen atom arranged
1-C
6-haloalkyl, at least one Y substituting group is-CF
3
-position to replacing on the 2-pyridyl, the 2-pyridyl is in 3-and/or 5-position.
Better, at the 5-bit substituent be-CF
3
According to the present invention, " Het " of general formula (I) compound can be 5-unit non-condensed heterocycle.Het is that the object lesson of 5-unit heterocyclic The compounds of this invention comprises:
*Het represents the heterocycle of general formula (II),
Wherein:
-R
2And R
3Can be identical or different, can be hydrogen atom, halogen atom, amino, nitro, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl;
-R
4Be hydrogen atom, halogen atom, nitro, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl.
*Het represents the heterocycle of general formula (III),
Wherein:
-R
5Be hydrogen atom, halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl;
-R
6And R
7Can be identical or different, be hydrogen atom, halogen atom, amino, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl.
*Het represents the heterocycle of general formula (IV),
Wherein:
-R
8Be halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl;
-R
9Be hydrogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl.
*The heterocycle of the logical formula V of Het representative,
Wherein:
-R
10And R
11Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-haloalkyl, C
1-C
4-alkylthio, C
1-C
4-alkyl sulphonyl, optional by halogen atom or C
1-C
4The phenyl that-alkyl replaces, or optional by halogen atom or C
1-C
4The pyridyl that-alkyl replaces;
-R
12Be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-haloalkyl or the C of 1-5 halogen atom is arranged
1-C
4-halogenated alkoxy.
*Het represents the heterocycle of general formula (VI),
Wherein:
-R
13And R
14Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl, C
1-C
4-alkoxyl group or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
15Be hydrogen atom, halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl.
*Het represents the heterocycle of general formula (VII),
Wherein:
-R
16Be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
17And R
19Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl;
-R
18Be hydrogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxy-C
1-C
4-alkyl, hydroxyl-C
1-C
4-alkyl, C
1-C
4-alkyl sulphonyl, two (C
1-C
4-alkyl) amino-sulfonyl, C
1-C
6-alkyl-carbonyl, optional by halogen atom or C
1-C
4The phenyl sulfonyl that-alkyl replaces, or halogen atom or C
1-C
4The benzoyl that-alkyl replaces.
*Het represents the heterocycle of general formula (VIII),
Wherein:
-R
20Be hydrogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxy-C
1-C
4-alkyl, hydroxyl-C
1-C
4-alkyl, C
1-C
4-alkyl sulphonyl, two (C
1-C
4-alkyl) amino-sulfonyl, C
1-C
6-alkyl-carbonyl, optional by halogen atom or C
1-C
4The phenyl sulfonyl that-alkyl replaces, or optional by halogen atom or C
1-C
4The benzoyl that-alkyl replaces;
-R
21, R
22And R
23Can be identical or different, be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl or C
1-C
4-alkyl-carbonyl.
*Het represents the heterocycle of general formula (IX),
Wherein:
-R
24Be hydrogen atom or C
1-C
4-alkyl;
-R
25Be halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl.
*Het represents the heterocycle of general formula (X),
Wherein:
-R
26Be hydrogen atom or C
1-C
4-alkyl;
-R
27Be halogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, or optional by halogen atom or C
1-C
4The phenyl that alkyl replaces.
*Het represents the heterocycle of general formula (XI),
Wherein:
-R
28Be hydrogen atom, halogen atom, amino, cyano group, C
1-C
4-alkylamino, two-(C
1-C
4-alkyl) amino, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, or optional by halogen atom or C
1-C
4The phenyl that alkyl replaces;
-R
29Be halogen atom, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl.
*Het represents the heterocycle of general formula (XII),
Wherein:
-R
30Be hydrogen atom, halogen atom, amino, cyano group, C
1-C
4-alkylamino, two-(C
1-C
4-alkyl) amino, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
31Be halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl.
*Het represents the heterocycle of general formula (XIII),
Wherein:
-R
32Be hydrogen atom, halogen atom, cyano group, nitro, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
3-C
6-cycloalkyl, C
1-C
4-alkoxyl group has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio, aminocarboxyl or aminocarboxyl-C
1-C
4-alkyl;
-R
33Be hydrogen atom, halogen atom, cyano group, nitro, C
1-C
4-alkyl, C
1-C
4-alkoxyl group or C
1-C
4-alkylthio;
-R
34Be hydrogen atom, phenyl, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, hydroxyl-C
1-C
4-alkyl, C
2-C
6-thiazolinyl, C
3-C
6-cycloalkyl, C
1-C
4-alkylthio-C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-halogenated alkylthio-C
1-C
4-alkyl, C
1-C
4-alkoxy-C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4-halogenated alkoxy-C
1-C
4-alkyl.
*Het represents the heterocycle of general formula (XIV),
Wherein:
-R
35Be hydrogen atom, halogen atom, cyano group, nitro, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
3-C
6-cycloalkyl, C
1-C
4-alkoxyl group has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio, aminocarboxyl or aminocarboxyl-C
1-C
4-alkyl;
-R
36Be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl, C
1-C
4-alkoxyl group has the C of 1-5 halogen atom
1-C
4-halogenated alkoxy, or C
1-C
4-alkylthio;
-R
37Be hydrogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, hydroxyl-C
1-C
4-alkyl, C
2-C
6-thiazolinyl, C
3-C
6-cycloalkyl, C
1-C
4-alkylthio-C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-halogenated alkylthio-C
1-C
4-alkyl, C
1-C
4-alkoxy-C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-halogenated alkoxy-C
1-C
4-alkyl, or optional by halogen atom, C
1-C
4-alkyl, C
1-C
4The phenyl that-alkoxyalkyl or nitro replace.
*Het represents the heterocycle of general formula (XV),
Wherein:
-R
38Be hydrogen atom, halogen atom, cyano group, nitro, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
3-C
6-cycloalkyl, C
1-C
4-alkoxyl group has the C of 1-5 carbon atom
1-C
4-halogenated alkoxy, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio, aminocarboxyl, or aminocarboxyl-C
1-C
4-alkyl;
-R
39Be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
40Be hydrogen atom, phenyl, benzyl, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, hydroxyl-C
1-C
4-alkyl, C
2-C
6-thiazolinyl, C
3-C
6-cycloalkyl, C
1-C
4-alkylthio-C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-halogenated alkylthio-C
1-C
4-alkyl, C
1-C
4-alkoxy-C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-halogenated alkoxy-C
1-C
4-alkyl.
*Het represents the heterocycle of general formula (XVI),
Wherein:
-R
41And R
42Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl.
*Het represents the heterocycle of general formula (XVII),
Wherein:
-R
43And R
44Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, optional by halogen atom or C
1-C
4The phenyl that alkyl replaces, optional by halogen atom or C
1-C
4The heterocyclic radical that alkyl replaces.
*Het represents the heterocycle of general formula (XVIII),
Wherein:
R
45And R
46Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl.
*Het represents the heterocycle of general formula (XIX),
Wherein:
-R
47Be halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl.
*Het represents the heterocycle of general formula (XX),
Wherein:
-R
48Be halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
49Be hydrogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-haloalkyl, or optional by halogen atom or C
1-C
4The phenyl that alkyl replaces.
*Het represents the heterocycle of general formula (XXI),
Wherein:
-R
50Be halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl.
According to the present invention, " Het " of general formula (I) compound is 6-unit non-condensed heterocycle.Wherein Het is that the object lesson of 6-unit heterocyclic The compounds of this invention comprises:
*Het represents the heterocycle of general formula (XXII),
Wherein:
-R
51Be hydrogen atom, halogen atom, hydroxyl, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio or the C of 1-5 halogen atom is arranged
1-C
4-halogenated alkoxy;
-R
52, R
53And R
54Can be identical or different, be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Alkoxyl group, C
1-C
4-alkyl sulfinyl, or C
1-C
4-alkyl sulphonyl.
*Het represents the heterocycle of general formula (XXIII),
Wherein:
-R
55Be hydrogen atom, halogen atom, hydroxyl, cyano group, amino, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
5-alkylthio, C
2-C
5-alkenylthio group has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, optional by halogen atom or C
1-C
4The phenoxy group that alkyl replaces, or optional by halogen atom or C
1-C
4The thiophenyl that alkyl replaces;
-R
56, R
57And R
58Identical or different, be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, C
1-C
4-alkyl sulfinyl, C
1-C
4-alkyl sulphonyl or optional by halogen atom or C
1-C
4The N-morpholine that alkyl replaces, or optional by halogen atom or C
1-C
4The thienyl that alkyl replaces.
*Het represents the heterocycle of general formula (XXIV),
Wherein:
R
59, R
60, R
61And R
62Can be identical or different, be hydrogen atom, halogen atom, hydroxyl, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, C
1-C
4-alkyl sulfinyl, or C
1-C
4-alkyl sulphonyl.
*Het represents the heterocycle of general formula (XXV),
Wherein:
-R
63Be hydrogen atom, halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
64Be hydrogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
6-alkoxy carbonyl, the optional benzyl that is replaced by 1-3 halogen atom, the optional benzyloxycarbonyl that is replaced by 1-3 halogen atom, or heterocyclic radical.
*Het represents the heterocycle of general formula (XXVI),
Wherein:
-R
65Be hydrogen atom, halogen atom, hydroxyl, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio or the C of 1-5 halogen atom is arranged
1-C
4-halogenated alkoxy;
-R
66Be hydrogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl or benzyl.
*Het represents the heterocycle of general formula (XXVII),
Wherein:
-X
1Be sulphur atom ,-SO-,-SO2-or-CH
2-;-R
67Be C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
68And R
69Can be identical or different, be hydrogen atom or C
1-C
4-alkyl.
*Het represents the heterocycle of general formula (XXVIII),
Wherein:
-R
70Be C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl.
*Het represents the heterocycle of general formula (XXIX),
Wherein:
-R
71Be C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl.
*Het represents the heterocycle of general formula (XXX),
Wherein:
-R
72Be hydrogen atom, halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl.
The invention still further relates to the method for preparing general formula (I) compound.Therefore, according to a further aspect of the invention, provide to prepare the method for general formula (1) compound as mentioned above, this method comprises: the carboxylic acid derivative that makes general formula (A)
Wherein:
-Het is by top definition;
-G is a halogen atom, hydroxyl or C
1-C
6-alkoxyl group,
With the 2-pyridine derivate reaction of general formula (B), if G is hydroxyl or C
1-C
6-alkoxyl group carries out in the presence of catalyzer, if G is a halogen atom, in the presence of acid binding agent, carries out,
Wherein, Y, R
1Press top definition with n.
According to the present invention, if G is hydroxyl or C
1-C
6-alkoxyl group is prepared general formula (1) compound method in the presence of catalyzer.Appropriate catalyst comprises the coupling reagent dicyclohexylcarbodiimide, N, N '-carbonyl dimidazoles, phosphofluoric acid bromo tripyrrole Wan Ji Phosphonium and trimethyl aluminium.
According to the present invention, if G is a halogen atom,, in the presence of acid binding agent, be prepared the method for general formula (1) compound.Suitable acid binding agent comprises carbonate, buck or tertiary amine.
The invention still further relates to the another kind of method of preparation general formula (I) compound.Therefore, according to another aspect of the invention, provide second kind to prepare the method for general formula (I) compound as mentioned above, this method comprises: make the carboxylic acid anhydride of general formula (C),
Wherein:
-Het is by top definition;
-W presses Het definition or C
1-C
6-alkyl;
With general formula (D) 2-pyridine derivate, reaction in the presence of reductive agent,
Wherein: R
1Press top definition separately with n.
According to the present invention, the second method of preparation general formula (I) compound is carried out in the presence of reductive agent.Suitable reductive agent comprises H
2And NaBH
4
The compounds of this invention can be according to above-mentioned universal method preparation.However, it should be understood that those skilled in the art can be applicable to this method needs the synthetic special compound in this compounds.For example, if suitably, aforesaid method carries out in the presence of thinner.If suitably, also can be at catalyzer such as NiCl
2-H
2O or CoCl
3-H
2There is the second kind of preparation method who carries out general formula (I) compound down in O.
Some midbody compounds that are used to prepare general formula (I) compound are novel.Therefore, the invention still further relates to the novel intermediates compound that is used to prepare general formula (I) compound.Therefore, according to the present invention, provide the compounds of general formula (E):
Wherein:
-Z can be identical or different, is halogen atom, nitro, cyano group, hydroxyl, carboxyl, C
1-C
8-alkyl has the C of 1-5 halogen atom
1-C
6-haloalkyl has the C of 1-5 halogen atom
1-C
6-halogenated alkoxy, C
1-C
8-alkylthio has the C of 1-5 halogen atom
1-C
6-halogenated alkylthio, C
2-C
8-alkene oxygen base has the C of 1-5 halogen atom
2-C
8-haloalkene oxygen base, C
3-C
8-alkynyloxy group has the C of 1-5 halogen atom
3-C
8-halo alkynyloxy group, C
3-C
8-cycloalkyl, C
1-C
8-alkoxy carbonyl, C
1-C
8-alkyl sulfinyl, C
1-C
8-alkyl sulphonyl has the C of 1-5 halogen atom
1-C
8-haloalkyl sulfinyl has the C of 1-5 halogen atom
1-C
8-haloalkyl-alkylsulfonyl or C
1-C
6-Alkoximino-C
1-C
6-alkyl;
-Z
1Be halogen atom or C
1-C
8-alkyl;
-R
1Press top definition with n.
The invention still further relates to the fungicide composition that comprises significant quantity general formula (I) active substance.Therefore, according to the present invention, provide a kind of fungicide composition, said composition comprises general formula defined above (I) compound of significant quantity as active ingredient, and agricultural goes up acceptable carrier or weighting agent.
In this specification sheets, term " carrier " is meant natural or synthetic, organic or inorganic material, and they and active substance mix, and makes on the part of their easier paint plants.This carrier is inert normally, should be that agricultural is upward acceptable.Described carrier can be solid or liquid.Suitable upholder example comprises clay, natural or synthetic silicate, silicon oxide, resin, wax, solid fertilizer, water, alcohols (especially butanols), organic solvent, inorganic and vegetables oil and their derivative thereof.Also can use the mixture of this carrier.
Described composition also comprises other component.Especially, described composition also comprises surfactant.Described tensio-active agent can be emulsifying agent, dispersion agent or the wetting agent of ionic or non-ionic type, perhaps this surfactant mixtures.Mentioned phosphoric acid ester, the fatty acid ester of polyvalent alcohol and the derivative that comprises vitriol, sulfonate and the functional above-claimed cpd of phosphoric acid salt of salt, taurine derivatives (especially taurine alkyl ester), Volpo S 10 or phenol of phenol (especially alkylphenol or aryl phenol), the sulfosuccinic ester of polycondensate, the replacement of for example polyacrylate, Sulfite lignin, benzene sulfonate or naphthalenesulfonate, oxyethane and Fatty Alcohol(C12-C14 and C12-C18) or lipid acid or aliphatic amide.Water insoluble when active substance and/or inert support, and must there be at least a tensio-active agent in the described carrier that applies usefulness when being water usually.Be preferably, the content of tensio-active agent accounts for the 5-40 weight % of described composition.
Randomly, also can add other component, for example, protective colloid, tackiness agent, thickening material, thixotropic agent, permeate agent, stablizer, sequestrant.Be more preferably, described active substance can mix with any solid or fluid additive, and they conform to general compounding process.
Usually, composition of the present invention comprises the active substance of 0.05-99 weight %, better is 10-70 weight %.
Composition of the present invention can use with various forms, as aerosol dispersion, bait (stand-by), the bait enriched material, block bait, micro-capsule suspension, cold mist enriching agent, the agent of can dusting, but emulsion concentrate, O/w emulsion, water-in-oil emulsion, capsule granula, granula subtilis, the flowed enriching agent that seed treatment is used, gas (under pressure), the product of generation gas, grain bait, granular bait, granule, hot mist enriching agent, big granula, microgranules, can be dispersed in the powder in the oil, oil can mix the enriching agent that can flow, the agent of oil miscible fluids, paste, the plant spillikin, sheet bait is used for doing the pulvis of seed treatment, chip bait, the seed of coated pesticidal, the smog candle, aerosol bomb, aerosol producer, the smog bead, the smog spillikin, smog sheet, smoke candle, solubility concentrates agent, soluble powder, the solution that is used for seed treatment, suspension enriching agent (enriching agent can flow), the spike pulvis, ultra-low volume (ulv) liquor, ultra-low volume (ulv) suspension agent, released vapour product, but water dispersible granule or tablet, but be used for the water dispersion powder that slurries are handled, water-soluble granule or tablet, the water solube powder and the wettability pulvis that are used for seed treatment.
These compositions not only comprise by what appropriate device such as spraying plant or dusting device were handled and are administered to composition on plant or the seed easily, also be included in be administered to before the crop must dilution concentrated commercial composite.
Compound of the present invention also can be with one or more sterilants, mycocide, bactericide, lure the compound of miticide or pheromone or other biologically active.The compound that makes thus has wide activity profile.Mixture with other mycocide is especially favourable.
Mycocide of the present invention can be used for the treatment of or the preventative phytopathogenic fungi of preventing and treating crop.Therefore, according to a further aspect in the invention, the method of the phytopathogenic fungi of treatment or preventative control crop is provided, it is characterized in that, above-mentioned fungicide composition is administered in the fruit or plant-growth or its required soil of growing of seed, plant and/or plant.
Be used for the active substance shown in the general formula (I) that composition to the phytopathogenic fungi of crop comprises significant quantity and non-plant toxin amount.
Express the amount that " significant quantity and non-plant toxin amount " is meant the present composition, can be enough to prevent and treat or destroy the fungi that exists or easily on farm crop, occur on the crop, and can not bring any significant phytotoxic symptom described crop.According to the compound that comprises in the fungi that will control, agrotype, weather condition and the epiphyte composition of the present invention, this amount can change on a large scale.
This amount can determine that this is in those skilled in the art's limit of power by the field test of system.
Treatment process of the present invention can be used for handling reproductive material such as stem piece or rhizome, also can be seed, seedling or transplanting seedling and plant or transplanting plant.Described treatment process also can be used for handling root.Treatment process of the present invention also can be used for handling the doing of the over-ground part of plant such as relevant plant, stem or bar, leaf, flower and fruit.
Can shielded plant by the method for the invention, that can nominate has a cotton, flax, grape, the fruit crop such as the Rosaceae (Rosaceae sp.) are (for example, nuts and kernels fruit, as apple and pears, also comprise drupe, as apricot, almond and peach), tea bamboo trunk scarabaeidae (Ribesioidae sp.), Juglandaceae (Juglandaceae sp.), Betulaceae (Betulaceae sp.), Anacardiaceae (Anacardiaceae sp.), Fagaceae (Fagaceae sp.), Moraceae (Moraceae sp.), Oleaceae (Oleaceae sp.), Actinidiaceae (Actinidaceae sp.), Lauraceae (Lauraceae sp.), Musaceae (Musaceae sp.) (for example banana tree and powder bajiao banana), alizarin section (Rubiaceae sp.) early, Theaceae (Theaceae sp.), Sterculiaceae (Sterculiceae sp.), Rutaceae (Rutaceae sp.) (for example, lemon, orange and natsudaidai); Leguminous crop such as Solanaceae (Solanaceae sp.) (for example, tomato), Liliaceae (Liliaceae sp.), Aster tataricus section (Asteraceae sp.) (for example, lettuce), umbelliferae (Umbelliferae sp.), Cruciferae (Cruciferae sp.), Chenopodiaceae (Chenopodiaceaesp.), Curcurbitaceae (Cucurbitaceae sp.), butterfly section (Papilionaceae sp.) (for example, pea), the Rosaceae (for example, strawberry); Large-scale crop, as Gramineae (Graminae sp.) (for example, corn, cereal such as wheat, rice, barley and triticale), Aster tataricus section is (for example, Sunflower Receptacle), Cruciferae (for example, rape), butterfly section (for example, soybean), Solanaceae (for example, potato), Chenopodiaceae (for example, beet tails); Gardening and forest crop; And the genetic modification homologue of these crops.
Can be described as follows in the shielded Plant diseases by the inventive method:
-wheat, the seed disease that control is following: fusaridiosis (rotten little spore (Microdochium nivale) of snow and maize seedling damping-off (Fusarium roseum)), bunt (stinking smut of wheat (Tilletiacaries), dwarf bunt of wheat (Tilletia controversa) or India's bunt (Tilletiaindica)), septoria musiva disease (wheat leaf rot (Septoria nodorum)) and wheat glume blight;
-wheat, the disease of the gas first portion of the following plant of control: cereal ring spot (Tapesia yallundae, Tapesia acuiformis), wheat class gaeumannomyces graminis disease (gaeumannomyce (Gaeumannomyces graminis)), root blight (machete sickle spore bacterium (F.culmorum), Fusarium graminearum (F.graminearum)), black patches disease (cereal rhizoctonia (Rhizoctonia graminis)), Powdery Mildew (standing grain class powdery mildew wheat specialized form (Erysiphegraminis forma specie tritici)), rust (orchardgrass bar shaped handle rust (Pucciniastriiformis) and concealment handle rust (Puccinia recondita)) and septoria musiva disease (wheat septoria (Septoria tritici) and clever withered septoria musiva);
-wheat and barley, control bacterium and virus disease, for example, the barley yellow mosaic;
-barley, prevent and treat following seed disease: reticulated mottle disease (stripe disease of barley (Pyrenophoragrarninea), net blotch of barley (pyrenophora teres) and root rotof flax (cochliobolussativus)), loose smut of barley (powder bacterium in naked (Ustilago nuda) and sickle spore bacterium disease (fusaria) (rotten little spore bacterium (Microdochium nivale) of snow and pink sickle spore bacterium (Fusarium roseum));
-barley, the disease of the gas first portion of the following plant of control: cereal ring spot (Tapesia yallundae), reticulated mottle disease (net blotch of barley (Pyrenophora teres) and root rotof flax (Cochliobolussativus)), Powdery Mildew (standing grain class powdery mildew wheat specialized form), betel rust (barley dwell rest fungus (Pucciniahordei)) and leaf spot (barley leaf blotch (Rhynchosporium secalis));
-potato, (especially eggplant grows the spore (Helminthosporium Solani) of wriggling to the disease of control stem piece, Tuberose stem point mould (Phoma tuberosa), Malin's potato damping-off (Rhizoctonia solani), rice seedling damping-off (Fusarium solani)), mildew (Malin's potato late blight (Phytopthora Infestans)) and some virus (viral Y);
-potato prevents and treats following leaf disease: early blight (potato black spot (Alternaria olani)), mildew (phytophthora infestans (Phytophthora infestans));
-cotton, the following sapling growth disease of control: samping off and neck rot (dry thread Pyrenomycetes (Rhizoctonia solani), fusarium wilt of sweet potato (Fusarium oxysporum)) and black root rot (black root rot of sweet potato (Thielaviopsis basicola)) from seed;
-produce proteinic crop, for example, pea, prevent and treat following seed disease: anthrax (pea brown spot (Ascochyta pisi), pea black spot (Mycosphaerella pinodes)), fusaridiosis (sharp sickle spore bacterium (Fusarium oxysporum)), gray mold (Botrytis cinerea bacterium (Botrytis cinerea)) and mildew (pea oidium (Peronospora pisi));
-oil-containing crop, for example rape is prevented and treated following seed disease: Cruciferae root branch disease (Phoma lingam), Kidney bean leaf blight (Alterniaria brassicae) and sclerotinia rot of colza (Sclerotiniasclerotiorum);
-corn, control seed disease: (Rhizopus (Rhizopus Sp.), penicillin belongs to (PenicilliumSp.), Trichoderma (Trichoderma Sp.), Aspergillus (Aspergillus Sp.) and gibberella fujikuroi (Gibberella fujikuroi));
-flax, control seed disease: flax gives birth to chain lattice spores (Alterniaria Linicola);
-trees prevent and treat samping off (fusarium wilt of sweet potato, rhizoctonia rot of cotton);
-rice is prevented and treated the disease with therapeutic method to keep the adverse qi flowing downward first portion: blight (the huge seat of ash shell (Magnaporthe grisea)), the sheath and culm blight of rice (Rhizoctonia solani);
-leguminous crop is prevented and treated following seed or from the disease of the sapling of seed: samping off and neck rot (sharp sickle spore bacterium, pink sickle spore bacterium, dry thread Pyrenomycetes, pythium (Pythium sp.));
-leguminous crop, control is with the disease of therapeutic method to keep the adverse qi flowing downward first portion: gray mold (Staphlosporonites (Botrytis sp.)), Powdery Mildew (tobacco Powdery Mildew (Erysiphe cichoracearum) especially, cucurbits powdery mildew (Sphaerotheca fuliginea) and powdery mildew of cucumber (Leveillula Taurica), sickle spore bacterium disease (fusaria) (sharp sickle spore bacterium, pink sickle spore bacterium), leaf spot (Cladosporium (Cladosporium sp.)), chain lattice spore tikka is (the lattice spore belongs to (Alternaria sp.)) also, anthrax (jute is deceived anthrax (Colletotrichumsp.)), the septoria musiva tikka is (Septoria (Septoriasp.)) also, black spot (dry thread Pyrenomycetes), mildew (for example, lettuce frost (Bremia lactucae), Peronospora (Peronospora sp.), satin Peronospora (Pseudoperonospora sp.), phytophthora (Phytophthora sp.));
-fruit tree, the disease of gas first portion: brown heart (pears brown heart (Monilia fructigenae), plum brown heart (M.laxa)), incrustation (scab of apple (Venturia inaequalis), Powdery Mildew (apple mildew (Podosphaera leucotricha));
-grapevine, the disease of control leaf: gray mold (Botrytis cinerea bacterium (Botrytis cinerea)) especially, Powdery Mildew (uncinula necator (Uncinula necator)), Black Rotten (bitter rot or anthracnose of grape (Guignardiabiwelli)) and mildew (downy mildew of garpe (Plasmopara viticola));
-beet tails, control is with the disease of therapeutic method to keep the adverse qi flowing downward first portion: the mould blight of tail spore (beet cercospora leaf spot (Cercosporabeticola)), Powdery Mildew (beet powdery mildew (Erysiphe beticola)), leaf spot (beet spot disease (Ramularia beticola)).
Fungicide composition of the present invention also can be used for treating dependence and grows on the timber or interior fungal disease.Term " timber " is meant all types of timber, all types of workpiece of the timber that is used to build, for example, solid wood, high-density timber, cord-wood and glued board.Handling the method for timber of the present invention mainly is made up of following steps: contact one or more compounds of the present invention or composition of the present invention.This for example comprises and directly applies, sprays, floods, sprays or other suitable method arbitrarily.
The dosage of the present invention's used active substance in handling better is 10-800g/ha usually, for foliage applying, better is 50-300g/ha.When carrying out seed treatment, the dosage of used active substance better is every 100kg seed 2-200g usually, better is every 100kg seed 3-150g.Clearly, above-mentioned dosage is as exemplary embodiment of the present invention.How those skilled in the art are known adopts application dosage according to be processed as properties.
Fungicide composition of the present invention also can be used in the organism of using The compounds of this invention or agrochemical composition of the present invention treatment genetic modification.The plant of genetic modification is will encode the heterologous gene stable integration of proteins of interest matter to its genomic plant.The described statement heterologous gene of matter " coding proteins of interest " is to show to transform the gene that plant provides new agricultural character basically, perhaps improves the gene of the agricultural quality of described conversion plant.
Composition of the present invention also can be used for preparation treatment or preventative processing human and animal's fungal disease such as mycosis, tetter, tinea capitis, moniliosis or by Aspergillus, for example the composition of the disease that causes of Aspergillus fumigatus.
Now, compound and the embodiment with reference to following table illustrates feature of the present invention.Following Table A and B have illustrated Fungicidal compounds of the present invention in nonrestrictive mode.In following examples, M+1 (or M-1) is meant the molecular ion peak that adds or deduct 1a.m.u (atomic mass unit) respectively, observed as mass spectroscopy, M (ApcI+) is meant molecular ion peak, as finding in mass spectroscopy by positive normal atmosphere chemical ioni zation.
Table A
Table B
Table C
Table D
Table E
Table F
Table G
Table H
Table I
Table J
Table K
Table L
Table M
Table N
Table O
Table P
Table Q
Table R
Table S
Table T
Table U
Table V
The embodiment of preparation general formula (I) compound
Embodiment A:
Preparation N-[2-(3-chloro-5-trifluoromethyl-pyridine-2-yl)-ethyl-2-trifluoromethyl-niacinamide
Stirring at room 204mg (1mmol) 2-trifluoromethyl nicotinic acid, 200mg (0.9mmol) 2-(3-chloro-5-trifluoromethyl-pyridine-2-yl)-ethamine and 620mg (1.3mmol) bromo tripyrrole alkane phosphonium hexafluorophosphate and 230mg (1.8mmol) N, the 8ml dichloromethane solution of N-diisopropylethylamine 20 hours.
Mixture dilutes with 10ml water, and after the separation, methylene dichloride is used saturated NH mutually
4Cl solution and water washing.The organic phase dried over sodium sulfate.Behind the evaporating solvent, resistates is by purification by silica gel column chromatography (elutriant: hexane/ethyl acetate=10: 1 to 1: 1).Productive rate: 370mg (98%).
Embodiment B:
Preparation 2-chloro-N-[2-(3-chloro-5-trifluoromethyl-pyridine-2-yl)-ethyl-C-methyl-niacinamide
Stirring at room 161mg (0.7mmol) 2-chloro-6-methyl nicotinoyl chlorine, the 8ml acetonitrile solution of 160mg (0.7mmol) 2-(3-chloro-5-trifluoromethyl-pyridine-2-yl)-ethylamine hydrochloride and 236mg (1.7mmol) yellow soda ash 3 days.
Mixture is diluted with 5ml water and 5ml ethyl acetate, after the separation, the saturated NH of organic phase
4Cl solution and water washing.Organic phase dried over sodium sulfate, and evaporation.Productive rate: 200mg (62%).
Embodiment C:
Preparation 1-methyl-3-Trifluoromethyl-1 H-pyrazoles-4-carboxylic acid [2-(3-chloro-5-trifluoromethyl-pyridine-2-yl)-ethyl]-acid amides
At 0 ℃, 132mg (3.5mmol) sodium borohydride branch is joined 370mg (1.0mmol) 1-methyl-3-Trifluoromethyl-1 H-pyrazoles-4-carboxylic acid anhydride in small batches, in 110mg (0.5mmol) (3-chloro-5-trifluoromethyl-pyridine-2-yl)-acetonitrile and the hexahydrated 5ml acetonitrile solution of 120mg (0.5mmol) nickelous chloride (II).Continue under the room temperature to stir 4 hours.
Behind the evaporating solvent, resistates is by purification by silica gel column chromatography (elutriant: hexane/ethyl acetate=10: 1 to 1: 1).Productive rate: 80mg (40%).
The biological activity embodiment of general formula (I) compound
Embodiment 1: the activity in vivo test of alternaria (Alternaria brassicae) (Cruciferae leaf spot (Leaf Spotof Crucifers)):
Use the pottery homogenizing, prepare the active ingredient of testing in the concentrated suspension type preparation of 100g/l.This suspension is dilute with water then, meets the requirements of active material concentration.
Radish in the seed cup (radish) plant (Pernot kind) is sowed on 50/50 peat soil-volcanic ash substrate, 18-22 ℃ of growth down.Handle in the cotyledon stage by spraying above-mentioned waterborne suspension.
Spray control plant with the aqueous solution that does not contain this active substance.
After 24 hours, (40000 spores/ml) infect described plant with the alternaria spore.Collect spore from the biggest culture of 12-13.
In humid atmosphere, the radish plant that maintenance is infected under 18-20 ℃ 6-7 days.
After infecting 6-7 days, compare with control plant and to carry out classification.
Under these conditions, observe and use following compound, with 330ppm dosage, it always protects respond well (at least 50%): A-3, A-4, B-2, B-4, B-5; B-7, B-8, B-9, B-10, B-13, B-14, B-16, C-2; C-3, C-5, C-6, C-8, C-12, C-13, C-14, C-16; C-18, C-21, C-23, D-4, D-5, E-3, E-4, F-3; G-1, H-1, H-2, H-4, H-6, H-7, H-17, H-19; H-22, H-23, I-1, I-3, J-1, J-2, J-3, J-4; J-5, J-6, J-12, J-13, J-19, J-22, J-24, J-25; J-26, J-31, J-32, J-33, J-35, J-36, J-37, J-38; J-39, J-41, J-43, J-45, J-47, J-49, J-50; J-51, J-52, J-53, J-55, K-3, K-6, M-2; M4, M-5, M-6, N-1, O-1, Q-1, Q-2; R-1, R-5, R-6, R-7, R-10, R-11, R-13; R-14, R-15, R-23, R-24, R-26, R-30, R-31; S-2, S-5, V-1, V-6, V-7, V-8, V-12.
Embodiment 2: to the activity in vivo test of wheat powdery mildew (Erysiphe eraminis f.sp.Tritici) (wheat powdery mildew (wheatpowdery mildew))
Use the pottery homogenizing, prepare the active ingredient of testing in the concentrated suspension type preparation of 100g/l.This suspension is dilute with water then, meets the requirements of active material concentration.
Audace kind wheat plant in the seed cup is sowed on 50/50 peat soil-volcanic ash substrate, 12 ℃ of growths down.Handle in the 1-leaf stage (10cm height) by spraying above-mentioned waterborne suspension.
Spray control plant with the aqueous solution that does not contain this active substance.
After 24 hours, use ill plant to sow the wheat powdery mildew spore powder, infect described plant.
After infecting 7-14 days, compare with control plant and to carry out classification.
Under these conditions, observe and use following compound, with 330ppm dosage, it always protects respond well (at least 50%): A-4, B-4, B-8, C-2; C-3, C-12, D-4, F-1, H-1, H-2, H-4; H-20, I-3, J-1,, J-2, J-3; J-19, J-20, J-31, J-37, J-40, J-55; J-57, J-58, J-59, J-61, K-1, M-5; M-6, R-1, R-10, R-26, R-29, V-7.
Embodiment 3: to the activity in vivo test of Botrytis cinerea bacterium (Botrytis cinerea) (gray mold of cucumber (cucumber Greymould))
Use the pottery homogenizing, prepare the active ingredient of testing in the concentrated suspension type preparation of 100g/l.This suspension is dilute with water then, meets the requirements of active material concentration.
Marketer kind cucumber plant in the seed cup is sowed on 50/50 peat soil-volcanic ash substrate, 12 ℃ of growths down.Handle in the Z11 stage by spraying above-mentioned waterborne suspension.Handle control plant with the aqueous solution that does not contain this active substance.
After 24 hours, (150,000 spores/ml) drop is deposited on the blade face upper surface, infects described plant with the suspension liquid of aqueous phase of Botrytis cinerea bacterium spore.Collect spores and be suspended in the nutritive medium of forming by following component from 15 cultures of the biggest:
The 20g/l white glues
50g/l sucrose
2g/l?NH
4NO
3
1g/l?KH
2PO
4
The cucumber plant that infects was the indoor sedimentation of the artificial environment of 15-11 ℃ (day/night) and 80% relative humidity 5/7 day.
After infecting 5/7 day, compare with control plant and to carry out classification.Under these conditions, observe and use following compound, with 330ppm dosage, it always protects respond well (at least 50%): B-7, B-8, B-13, B-14, C-3; C-12, C-13, C-14, C-15, C-16, D-4, D-5; E-4, H-1, H-2, H-4, H-7, H-9, H-22; J-1, J-2, J-3, J-19, J-31, J-32, J-33; J-34, J-35, J-37, J-39, J-43, J-44, R-1; R-10, R-23, R-24, R-26, R-31, V-1, V-8.
Embodiment 4: the activity in vivo to net blotch of barley bacterium (Pyrenophora teres) (net blotch of barley (Barley Netblotch)) is tested:
Use the pottery homogenizing, the test active ingredient of preparation in the concentrated suspension type preparation of 100g/l.This suspension is dilute with water then, meets the requirements of active material concentration.
Express kind barley plants in the seed cup is sowed on 50/50 peat soil-volcanic ash substrate, 12 ℃ of growths down.Handle in the 1-leaf stage (10cm height) by spraying above-mentioned waterborne suspension.Handle control plant with the aqueous solution that does not contain this active substance.
After 24 hours, spray suspension liquid of aqueous phase (120,000 spores/ml), infect described plant of net blotch of barley bacterium spore.Collect spore from 12 the biggest cultures.The barley plants that infects was cultivated 24 hours under 20 ℃ and 100% relative humidity, then 80% relative humidity cultivation 12 days.
After infecting 12 days, compare with control plant and to carry out classification.Under these conditions, observe and use following compound, with 330ppm dosage, always protect respond well (at least 50%): A-4, B-3, B-7, B-8, B-13; B-14, B-15, B-16, C-3, C-5, C-12, C-13, C-14; C-15, C-16, C-17, C-20, C-22, C-23, D-4; D-5, E-3, E-4, F-3, G-1, H-1, H-2; H-4, H-5, H-6, H-7, H-8, H-11, H-15; H-17, H-19, H-20, H-22, H-23, I-1,1-3; J-1, J-2, J-3, J-7, J-8, J-10, J-19; J-20, J-22, J-23, J-24, J-25, J-26, J-31; .J-32, J-33, J-34, J-35, J-36, J-37, J-39; J-40, J-41, J-42, J-43, J-44, J-46, J-49; J-50, J-51, J-52, J-54 .J-55, J-57, J-58; .J-59, J-61, K-6, M-4, P-1, R-1, R-9; R-10, R-14, R-15, R-23, R-26, R-30, R-31; S-2, V-1, V-7, V-8, V-11, V-12, V-13.
Embodiment 5: to Pseudoperonospora cubensis (test of the activity in vivo of Peronospora brassicae (wild cabbage oidium (Cabbage downymildew)):
Use the pottery homogenizing, the test active ingredient of preparation in the concentrated suspension type preparation of 100g/l.This suspension is dilute with water then, meets the requirements of active material concentration.
Eminence kind brassica oleracea plants in the seed cup is sowed on 50/50 peat soil-volcanic ash substrate, 18-20 ℃ of growth down.Handle in the cotyledon stage by spraying above-mentioned waterborne suspension.
Handle control plant with the aqueous solution that does not contain this active substance.
After 24 hours, spray waterborne suspension (50,000 spores/ml), infect described plant of Pseudoperonospora cubensis spore.Collect spore from infected plant.
The barley plants that infects was cultivated 5 days in 20 ℃ and humid atmosphere.
After infecting 5 days, compare with control plant and to carry out classification.
Under these conditions, observe and use following compound, with 330ppm dosage, always protect respond well (at least 50%): B-6, B-7, J-46, J-59.
Under these conditions; patent application WO 01/11965 (referring to the table D in 306; 307; 310; 315 and 316) the N-{1-ethylamino formyl radical of Jie Shiing-2-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl }-the 4-chlorobenzamide; N-{1-ethylamino formyl radical-2-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl }-the 3-nitrobenzamide; N-{1-ethylamino formyl radical-2-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl }-the 2-brombenzamide; N-{1-methylamino formyl radical-2-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl }-4-methoxy benzamide and N-{1-methylamino formyl radical-2-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl }-the 4-phenylbenzamaide; when 330ppm; alternaria and net blotch of barley bacterium are shown poor drug effect, Botrytis cinerea bacterium and Pseudoperonospora cubensis are not shown drug effect.
Under these conditions, N-{[3-chloro-5-(trifluoromethyl)-2-pyridyl that patent application WO01/11965 (referring to compound 101 among the table B) discloses]-methyl }-5-thienyl ethanamide, when 330ppm, alternaria is shown poor drug effect, Botrytis cinerea bacterium and Pseudoperonospora cubensis there are not drug effect.
Claims (21)
1. the compound of general formula (I):
Wherein:
-X is Sauerstoffatom or sulphur atom;
-Y can be identical or different, is halogen atom, nitro, cyano group, hydroxyl, carboxyl, C
1-C
8-alkyl has the C of 1-5 halogen atom
1-C
6-haloalkyl, C
1-C
8-alkylamino, two-C
1-C
8-alkylamino, C
1-C
8-alkoxyl group has the C of 1-5 halogen atom
1-C
6-halogenated alkoxy, C
1-C
8-alkylthio has the C of 1-5 halogen atom
1-C
6-halogenated alkylthio, C
2-C
8-alkene oxygen base has the C of 1-5 halogen atom
2-C
8-haloalkene oxygen base, C
3-C
8-alkynyloxy group has the C of 1-5 halogen atom
3-C
8-halo alkynyloxy group, C
3-C
8-cycloalkyl, C
1-C
8-alkoxy carbonyl, C
1-C
8-alkyl sulfinyl, C
1-C
8-alkyl sulphonyl has the C of 1-5 halogen atom
1-C
8-haloalkyl sulfinyl has the C of 1-5 halogen atom
1-C
8-halogenated alkyl sulfonyl, or C
1-C
6-Alkoximino-C
1-C
6-alkyl;
-R
1Be hydrogen atom, cyano group, nitro, formyl radical, C
1-C
6-alkyl, C
1-C
6-alkyl-carbamoyl, C
2-C
6-thiazolinyl, C
2-C
6-alkynyl has the C of 1-7 halogen atom
1-C
6-haloalkyl, C
1-C
6-alkoxy-C
1-C
6-alkyl, C
1-C
6-Qing Wanji, C
1-C
6-aminoalkyl group, C
3-C
6-cycloalkyl, C
1-C
6-alkyl-carbonyl has the C of 1-5 halogen atom
1-C
6-halogenated alkyl carbonyl, C
1-C
6-alkoxy-C
1-C
6-alkyl-carbonyl, C
1-C
6-alkyl alkylthio base, or the C of 1-5 halogen atom is arranged
1-C
6-haloalkyl sulfane base;
-n is 1,2,3 or 4;
The heterocycle of-Het representative (II),
Wherein:
-R
2And R
3Can be identical or different, be hydrogen atom, halogen atom, amino, nitro, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
4Be hydrogen atom, halogen atom, nitro, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl; Perhaps
The heterocycle of Het representative (III),
Wherein:
-R
5Be hydrogen atom, halogen atom, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
6And R
7Can be identical or different, be hydrogen atom, halogen atom, amino, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl; Perhaps
The heterocycle of Het representative (V),
Wherein:
-R
10And R
11Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkylthio, C
1-C
4-alkyl sulphonyl, optional by halogen atom or C
1-C
4The phenyl that-alkyl replaces, or optional by halogen atom or C
1-C
4The pyridyl that-alkyl replaces;
-R
12Be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, or the C of 1-5 halogen atom is arranged
1-C
4Halogenated alkoxy; Perhaps
The heterocycle of Het representative (VI),
Wherein:
-R
13And R
14Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl, C
1-C
4-alkoxyl group, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
15Be hydrogen atom, halogen atom, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl; Perhaps
The heterocycle of Het representative (VII),
Wherein:
-R
16Be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
17And R
19Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
18Be hydrogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxy-C
1-C
4-alkyl, hydroxyl-C
1-C
4-alkyl, C
1-C
4-alkyl sulphonyl, two (C
1-C
4-alkyl) amino-sulfonyl, C
1-C
6-alkyl-carbonyl, optional by halogen atom or C
1-C
4The phenyl sulfonyl that-alkyl replaces, or optional by halogen atom or C
1-C
4The benzoyl that-alkyl replaces; Perhaps
The heterocycle of Het representative (VIII),
Wherein:
-R
20Be hydrogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxy-C
1-C
4-alkyl, hydroxyl-C
1-C
4-alkyl, C
1-C
4-alkyl sulphonyl, two (C
1-C
4-alkyl) amino-sulfonyl, C
1-C
6-alkyl-carbonyl, optional by halogen atom or C
1-C
4The phenyl sulfonyl that-alkyl replaces, or optional by halogen atom or C
1-C
4The benzoyl that-alkyl replaces;
-R
21, R
22And R
23Can be identical or different, be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, or C
1-C
4-alkyl-carbonyl; Perhaps
The heterocycle of Het representative (X),
Wherein:
-R
26Be hydrogen atom, or C
1-C
4-alkyl;
-R
27Be halogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl or optional by halogen atom or C
1-C
4The phenyl that alkyl replaces; Perhaps
The heterocycle of Het representative (XI),
Wherein:
-R
28Be hydrogen atom, halogen atom, amino, cyano group, C
1-C
4-alkylamino, two-(C
1-C
4-alkyl) amino, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, or optional by halogen atom or C
1-C
4The phenyl that alkyl replaces;
-R
29Be halogen atom, C
1-C
4-alkyl or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl; Perhaps
The heterocycle of Het representative (XIII),
Wherein:
-R
32Be hydrogen atom, halogen atom, cyano group, nitro, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
3-C
6-cycloalkyl, C
1-C
4-alkoxyl group has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio, aminocarboxyl or aminocarboxyl-C
1-C
4-alkyl;
-R
33Be hydrogen atom, halogen atom, cyano group, nitro, C
1-C
4-alkyl, C
1-C
4-alkoxyl group or C
1-C
4-alkylthio;
-R
34Be hydrogen atom, phenyl, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, hydroxyl-C
1-C
4-alkyl, C
2-C
6-thiazolinyl, C
3-C
6-cycloalkyl, C
1-C
4-alkylthio-C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-halogenated alkylthio-C
1-C
4-alkyl, C
1-C
4-alkoxy-C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4-halogenated alkoxy-C
1-C
4-alkyl; Perhaps
The heterocycle of Het representative (XIV),
Wherein:
-R
35Be hydrogen atom, halogen atom, cyano group, nitro, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
3-C
6-cycloalkyl, C
1-C
4-alkoxyl group has the C of 1-5 halogen atom
1-C
4Alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio, aminocarboxyl or aminocarboxyl-C
1-C
4-alkyl;
-R
36Be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl, C
1-C
4-alkoxyl group has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, or C
1-C
4-alkylthio;
-R
37Be hydrogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, hydroxyl-C
1-C
4-alkyl, C
2-C
6-thiazolinyl, C
3-C
6-cycloalkyl, C
1-C
4-alkylthio-C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-halogenated alkylthio-C
1-C
4-alkyl, C
1-C
4-alkoxy-C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-halogenated alkoxy-C
1-C
4-alkyl, or optional by halogen atom or C
1-C
4Alkyl, C
1-C
4The phenyl that-alkoxyalkyl or nitro replace; Perhaps
The heterocycle of Het representative (XV),
Wherein:
-R
38Be hydrogen atom, halogen atom, cyano group, nitro, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
3-C
6-cycloalkyl, C
1-C
4-alkoxyl group has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio, aminocarboxyl, or aminocarboxyl-C
1-C
4-alkyl;
-R
39Be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
40Be hydrogen atom, phenyl, benzyl, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, hydroxyl-C
1-C
4-alkyl, C
2-C
6-thiazolinyl, C
3-C
6-cycloalkyl, C
1-C
4-alkylthio-C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-halogenated alkylthio-C
1-C
4-alkyl, C
1-C
4-alkoxy-C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-halogenated alkoxy-C
1-C
4-alkyl; Perhaps
The heterocycle of Het representative (XVI),
Wherein:
-R
41And R
42Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl; Perhaps
The heterocycle of Het representative (XVII),
Wherein:
-R
43And R
44Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, optional by halogen atom or C
1-C
4The phenyl that alkyl replaces, optional by halogen atom or C
1-C
4The heterocyclic radical that alkyl replaces; Perhaps
The heterocycle of Het representative (XVIII),
Wherein:
-R
45And R
46Can be identical or different, be hydrogen atom, halogen atom, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl; Perhaps
The heterocycle of Het representative (XX),
Wherein:
-R
48Be halogen atom, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
49Be hydrogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4-haloalkyl, or optional by halogen atom or C
1-C
4The phenyl that alkyl replaces; Perhaps
The heterocycle of Het representative (XXI),
Wherein:
R
50Be halogen atom, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl; Perhaps
The heterocycle of Het representative (XXII),
Wherein:
-R
51Be hydrogen atom, halogen atom, hydroxyl, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio, or the C of 1-5 halogen atom is arranged
1-C
4Halogenated alkoxy;
-R
52, R
53And R
54Can be identical or different, be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, C
1-C
4-alkyl sulfinyl, or C
1-C
4-alkyl sulphonyl; Perhaps
The heterocycle of Het representative (XXIII),
Wherein:
-R
55Be hydrogen atom, halogen atom, hydroxyl, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
5-alkylthio, C
2-C
5-alkenylthio group has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, optional by halogen atom or C
1-C
4The phenoxy group that alkyl replaces, or optional by halogen atom or C
1-C
4The thiophenyl that alkyl replaces;
-R
56, R
57And R
58, can be identical or different, be hydrogen atom, halogen atom, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, C
1-C
4-alkyl sulfinyl, C
1-C
4-alkyl sulphonyl, optional by halogen atom or C
1-C
4The N-morpholine that alkyl replaces, or optional by halogen atom or C
1-C
4The thienyl that alkyl replaces; Perhaps
The heterocycle of Het representative (XXIV),
Wherein:
R
59, R
60, R
61And R
62Can be identical or different, be hydrogen atom, halogen atom, hydroxyl, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkoxy, C
1-C
4-alkyl sulfinyl, or C
1-C
4-alkyl sulphonyl; Perhaps
The heterocycle of Het representative (XXV),
Wherein:
-R
63Be hydrogen atom, halogen atom, C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4-haloalkyl;
-R
64Be hydrogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
6-alkoxy carbonyl, the optional benzyl that is replaced by 1-3 halogen atom, the optional benzyloxycarbonyl that is replaced by 1-3 halogen atom, or heterocyclic radical; Perhaps
The heterocycle of Het representative (XXVI),
Wherein:
-R
65Be hydrogen atom, halogen atom, hydroxyl, cyano group, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkylthio has the C of 1-5 halogen atom
1-C
4Halogenated alkylthio, or the C of 1-5 halogen atom is arranged
1-C
4Halogenated alkoxy;
-R
66Be hydrogen atom, C
1-C
4-alkyl has the C of 1-5 halogen atom
1-C
4Haloalkyl or benzyl; Perhaps
The heterocycle of Het representative (XXVII),
Wherein:
-X
1Be sulphur atom ,-SO-,-SO
2-or-CH
2-;
-R
67Be C
1-C
4-alkyl, or the C of 1-5 halogen atom is arranged
1-C
4Haloalkyl;
-R
68And R
69Can be identical or different, be hydrogen atom or C
1-C
4-alkyl;
Het connects by carbon atom.
2. compound as claimed in claim 1 is characterized in that, the X represention oxygen atom.
3. compound as claimed in claim 1 is characterized in that, n is 1 or 2.
4. compound as claimed in claim 3 is characterized in that n is 2.
5. compound as claimed in claim 1 is characterized in that, at least one Y substituting group is a halogen atom, C
1-C
8-alkyl has the C of 1-5 halogen atom
1-C
6-haloalkyl, or C
1-C
6-alkoxy-C
1-C
6-alkyl-carbonyl.
6. compound as claimed in claim 5 is characterized in that, at least one Y substituting group is the C that 1-5 halogen atom arranged
1-C
6-haloalkyl.
7. compound as claimed in claim 6 is characterized in that, at least one Y substituting group is-CF
3
8. as each described compound among the claim 1-7, it is characterized in that the 2-pyridyl is substituted at 3-and/or 5-position.
9. compound as claimed in claim 8 is characterized in that, the 2-pyridyl is at 5-position quilt-CF
3Replace.
10. as each described compound among the claim 1-7, it is characterized in that Het is a 5-unit heterocycle.
11., it is characterized in that Het is a 6-unit heterocycle as each described compound among the claim 1-7.
12. a method for preparing arbitrary described general formula (I) compound among the claim 1-11, this method comprises:
Make general formula (A) carboxylic acid derivative:
Wherein:
-Het is by top definition;-G is a halogen atom, hydroxyl or C
1-C
6-alkoxyl group;
With the 2-pyridine derivate of general formula (B), if G is hydroxyl or C
1-C
6-alkoxyl group, in the presence of catalyzer, if or G be that halogen atom reacts in the presence of acid binding agent,
Wherein:
Y, R
1With n according to arbitrary described definition among the claim 1-11.
13. method as claimed in claim 12 is characterized in that, described catalyzer is a dicyclohexylcarbodiimide, N, N '-carbonyl dimidazoles, phosphofluoric acid bromo tripyrrole Wan Phosphonium, or trimethyl aluminium.
14. method as claimed in claim 13 is characterized in that, described acid binding agent is a carbonate, buck or quaternary amine.
15. a method for preparing arbitrary described general formula (I) compound among the claim 1-11, this method comprises:
Make general formula (C) carboxylic acid anhydride derivative,
Wherein:
-Het is by the arbitrary described definition of claim 1-11;
-W is by described Het definition or C
1-C
6-alkyl;
By the 2-pyridine derivate of carbonic acid (D), reaction in the presence of reductive agent
R
1Group is a hydrogen, and n defines according to claim 1.
16. method as claimed in claim 15 is characterized in that, reductive agent is H
2Or NaBH
4
17. the compound of general formula (E):
Wherein:
-Z can be identical or different, is halogen atom, nitro, cyano group, hydroxyl, carboxyl, C
1-C
8-alkyl has the C of 1-5 halogen atom
1-C
6-haloalkyl has the C of 1-5 halogen atom
1-C
6-halogenated alkoxy, C
1-C
8-alkylthio has the C of 1-5 halogen atom
1-C
6-halogenated alkylthio, C
2-C
8-alkene oxygen base has the C of 1-5 halogen atom
2-C
8-haloalkene oxygen base, C
3-C
8-alkynyloxy group has the C of 1-5 halogen atom
3-C
8-halo alkynyloxy group, C
3-C
8-cycloalkyl, C
1-C
8-alkoxy carbonyl, C
1-C
8-alkyl sulfinyl, C
1-C
8-alkyl sulphonyl has the C of 1-5 halogen atom
1-C
8-haloalkyl sulfinyl has the C of 1-5 halogen atom
1-C
8-haloalkyl-alkylsulfonyl, or C
1-C
6-Alkoximino-C
1-C
6-alkyl;
-Z
1Be halogen atom or C
1-C
8-alkyl;
-R
1Define according to claim 1 with n.
18. fungicide composition comprises among the claim 1-11 of significant quantity each described compound and agricultural and goes up acceptable carrier.
19. fungicide composition as claimed in claim 18 is characterized in that, described composition also comprises surfactant.
20. as claim 18 or 19 described fungicide compositions, described composition comprises the active substance of 0.05-99 weight %.
21. prevention or methods of treatment to the phytopathogenic fungi of crop, it is characterized in that, with claim 18-20 each described effectively and the composition that does not have a plant poison amount be administered on plant seed or plant leaf and/or the fruit, perhaps be administered in the required soil of the soil of plant-growth or plant-growth.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03356029.3 | 2003-02-19 | ||
| EP03356029A EP1449841A1 (en) | 2003-02-19 | 2003-02-19 | New fungicidal compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1751039A CN1751039A (en) | 2006-03-22 |
| CN100402525C true CN100402525C (en) | 2008-07-16 |
Family
ID=32731621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004800042371A Expired - Fee Related CN100402525C (en) | 2003-02-19 | 2004-02-12 | Pyridine derivatives as fungicidal compounds |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7754741B2 (en) |
| EP (2) | EP1449841A1 (en) |
| JP (1) | JP4630271B2 (en) |
| KR (1) | KR101084022B1 (en) |
| CN (1) | CN100402525C (en) |
| AT (1) | ATE497957T1 (en) |
| BR (1) | BRPI0406465B1 (en) |
| CA (1) | CA2516186C (en) |
| DE (1) | DE602004031326D1 (en) |
| ES (1) | ES2360627T3 (en) |
| IL (1) | IL169527A (en) |
| MX (1) | MXPA05008705A (en) |
| PL (1) | PL218548B1 (en) |
| WO (1) | WO2004074280A1 (en) |
| ZA (1) | ZA200504957B (en) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1548007A1 (en) * | 2003-12-19 | 2005-06-29 | Bayer CropScience S.A. | 2-Pyridinylethylcarboxamide derivatives and their use as fungicides |
| EP1574511A1 (en) * | 2004-03-03 | 2005-09-14 | Bayer CropScience S.A. | 2-Pyridinylethylcarboxamide derivatives and their use as fungicides |
| US20080033020A1 (en) * | 2004-07-23 | 2008-02-07 | Darren Mansfield | 3-Pyridinylethylbenzamide Derivatives as Fungicides |
| EP1771439A1 (en) * | 2004-07-23 | 2007-04-11 | Bayer CropScience S.A. | 4-pyridinylethylcarboxamide derivatives useful as fungicides |
| EP1794167A4 (en) * | 2004-09-10 | 2009-10-21 | Syngenta Ltd | Substituted isoxazoles as fungicides |
| EP1674455A1 (en) * | 2004-12-21 | 2006-06-28 | Bayer CropScience S.A. | Process for the preparation of a 2-ethylaminopyridine derivative |
| EP2518065A1 (en) * | 2005-04-08 | 2012-10-31 | Bayer CropScience AG | N-(furanylethyl)-heterocyclylcarboxamide derivatives as fungicides |
| MX2007014073A (en) * | 2005-05-13 | 2008-02-12 | Bayer Cropscience Sa | Fungicide 2-pyridyl-methylene-carboxamide derivatives. |
| EP1787981A1 (en) | 2005-11-22 | 2007-05-23 | Bayer CropScience S.A. | New N-phenethylcarboxamide derivatives |
| EP1792901A1 (en) | 2005-11-22 | 2007-06-06 | Bayer CropScience S.A. | N-(1-alkyl-2-phenylethyl)-carboxamide derivatives and use thereof as fungicides |
| TWI435863B (en) * | 2006-03-20 | 2014-05-01 | Nihon Nohyaku Co Ltd | N-2-(hetero) arylethylcarboxamide derivative and pest controlling |
| EP2029530B1 (en) | 2006-06-16 | 2012-09-19 | Syngenta Participations AG | Ethenyl carboxamide derivatives useful as microbiocides |
| US20100222219A1 (en) * | 2006-08-22 | 2010-09-02 | Basf Se | Thiophene-Sulphonic Acid Picolyl Amides |
| CL2007002787A1 (en) * | 2006-09-29 | 2008-05-30 | Bayer Cropscience Sa | COMPOUNDS DERIVED FROM N-CICLOALQUIL-CARBOXAMIDA, N-CICLOALQUIL-TIOCARBOXAMIDA AND N-CICLOALQUIL-CARBOXAMIDAMIDA N-SUBSTITUTED; FUNGICIDE COMPOSITION THAT INCLUDES SUCH COMPOUNDS; AND METHOD TO COMBAT FITOPATOGEN CULTURE FUNGIANS THAT YOU UNDERSTAND |
| AR064565A1 (en) * | 2007-01-03 | 2009-04-08 | Bayer Cropscience Sa | DERIVATIVES OF N-METILCARBOXAMIDE, A PROCEDURE FOR THEIR PREPARATION, A FUNGITIVE COMPOSITION THAT UNDERSTANDS THEM AND A METHOD FOR COMBATING FITOPATOGEN FUNDS THAT USES THEM. |
| JP5254957B2 (en) * | 2007-04-12 | 2013-08-07 | 日本農薬株式会社 | Nematicide composition and method of use thereof |
| CA2695331A1 (en) * | 2007-08-03 | 2009-02-12 | F. Hoffmann-La Roche Ag | Pyridinecarboxamide and benzamide derivatives as taar1 ligands |
| TWI504395B (en) | 2009-03-10 | 2015-10-21 | Substituted 3-amino-2-mercaptoquinoline as a KCNQ2 / 3 modifier | |
| TW201038565A (en) | 2009-03-12 | 2010-11-01 | Gruenenthal Gmbh | Substituted 2-mercapto-3-aminopyridines as KCNQ2/3 modulators |
| TWI475020B (en) | 2009-03-12 | 2015-03-01 | The substituted nicotine amide as a KCNQ2 / 3 modifier | |
| TWI461197B (en) | 2009-03-12 | 2014-11-21 | 2-mercaptoquinoline-3-carboxamide as a KCNQ2 / 3 modifier | |
| EP2564700A1 (en) * | 2009-03-25 | 2013-03-06 | Bayer CropScience AG | Nematicidal agent combinations comprising Fluopyram and Hirsutella |
| KR20130109940A (en) * | 2010-06-03 | 2013-10-08 | 바이엘 크롭사이언스 아게 | N-[(het)arylethyl] pyrazole(thio)carboxamides and their heterosubstituted analogues |
| PT2609083E (en) | 2010-08-27 | 2015-07-01 | Gruenenthal Gmbh | Substituted 2-oxy-quinoline-3-carboxamides as kcnq2/3 modulators |
| AR082733A1 (en) | 2010-08-27 | 2012-12-26 | Gruenenthal Gmbh | 2-AMINO-QUINOLINA-3-CARBOXAMIDS REPLACED AS MODULATORS OF KCNQ2 / 3 |
| PE20140214A1 (en) | 2010-08-27 | 2014-02-19 | Gruenenthal Chemie | 2-OXO- AND 2-THIOXO-DIHYDROQUINOLINE-3-CARBOXAMIDES SUBSTITUTED AS KCNQ2 / 3 MODULATORS |
| AU2011297937B2 (en) | 2010-09-01 | 2015-10-01 | Grunenthal Gmbh | Substituted 1-oxo-dihydroisoquinoline-3-carboxamides as KCNQ2/3 modulators |
| CN104023540A (en) * | 2011-11-02 | 2014-09-03 | 拜耳知识产权有限责任公司 | Compounds with nematicidal activity |
| EP2589292A1 (en) | 2011-11-02 | 2013-05-08 | Bayer CropScience AG | Compounds with nematicidal activity |
| EP2589294A1 (en) | 2011-11-02 | 2013-05-08 | Bayer CropScience AG | Compounds with nematicidal activity |
| EP2606728A1 (en) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | Compounds with nematicidal activity |
| US9301526B2 (en) | 2011-11-02 | 2016-04-05 | Bayer Intellectual Property Gmbh | Compounds with nematicidal activity |
| EP2606727A1 (en) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | Compounds with nematicidal activity |
| RU2638830C2 (en) | 2011-11-25 | 2017-12-18 | Байер Интеллектуэль Проперти Гмбх | Application of aryl and hetaryl carboxamides as endoparasiticides |
| CN104582702B (en) * | 2012-08-30 | 2018-07-10 | 国立大学法人东京大学 | Endoparasite control agent |
| EP2730570A1 (en) | 2012-11-13 | 2014-05-14 | Bayer CropScience AG | Pyridyloxyal alkyl carboxamides and their use as endoparasiticides and nematicide |
| UY35772A (en) | 2013-10-14 | 2015-05-29 | Bayer Cropscience Ag | NEW PESTICIDED COMPOUNDS |
| MX2016004533A (en) * | 2013-10-16 | 2016-07-22 | Bayer Cropscience Ag | N-cycloalkyl-n-(biheterocyclymethylene)-(thio)carboxamide derivatives. |
| JPWO2015125824A1 (en) | 2014-02-18 | 2017-03-30 | 日産化学工業株式会社 | Alkynylpyridine substituted amide compounds and pest control agents |
| CA2936886A1 (en) * | 2014-02-27 | 2015-08-03 | Merck Patent Gmbh | Heterocyclic compounds as nav channel inhibitors and uses thereof |
| US20230348392A1 (en) | 2020-05-06 | 2023-11-02 | Bayer Aktiengesellschaft | Pyridine (thio)amides as fungicidal compounds |
| CN111484448A (en) * | 2020-05-11 | 2020-08-04 | 中国农业科学院农业质量标准与检测技术研究所 | Fluopyram hapten, preparation method and application thereof, and antibody and method for detecting fluopyram |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1386965A (en) * | 1971-03-29 | 1975-03-12 | Aron Md Samuel J | 4-nitro pyridine -1- oxide derivatives nad compositions containing the same |
| WO2000021934A1 (en) * | 1998-10-15 | 2000-04-20 | Astrazeneca Ab | Compounds |
| CN1370047A (en) * | 1999-08-18 | 2002-09-18 | 阿方蒂农科有限公司 | Fungicides |
| CN1390204A (en) * | 1999-08-20 | 2003-01-08 | 道农业科学公司 | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1316667A (en) * | 1969-05-26 | 1973-05-09 | Xerox Corp | Benzobrazanquinone pigments |
| CA2036163C (en) * | 1990-02-14 | 2001-06-19 | Makoto Sunagawa | Novel beta-lactam compounds and their production |
| JP3005045B2 (en) * | 1990-02-14 | 2000-01-31 | 住友製薬株式会社 | Novel β-lactam compound and method for producing the same |
| AU687440B2 (en) * | 1993-08-24 | 1998-02-26 | Medivir Ab | Compounds and methods for inhibition of HIV and related viruses |
| FR2827286A1 (en) * | 2001-07-11 | 2003-01-17 | Aventis Cropscience Sa | New 3,4-disubstituted pyridine-2-carboxylic acid derivatives, useful as broad-spectrum plant fungicides and medicinal antifungal agents |
-
2003
- 2003-02-19 EP EP03356029A patent/EP1449841A1/en not_active Withdrawn
-
2004
- 2004-02-12 ES ES04710397T patent/ES2360627T3/en not_active Expired - Lifetime
- 2004-02-12 CN CNB2004800042371A patent/CN100402525C/en not_active Expired - Fee Related
- 2004-02-12 JP JP2006501983A patent/JP4630271B2/en not_active Expired - Fee Related
- 2004-02-12 WO PCT/EP2004/002381 patent/WO2004074280A1/en active Application Filing
- 2004-02-12 EP EP04710397A patent/EP1597252B1/en not_active Expired - Lifetime
- 2004-02-12 AT AT04710397T patent/ATE497957T1/en not_active IP Right Cessation
- 2004-02-12 MX MXPA05008705A patent/MXPA05008705A/en active IP Right Grant
- 2004-02-12 US US10/545,364 patent/US7754741B2/en not_active Expired - Fee Related
- 2004-02-12 KR KR1020057015235A patent/KR101084022B1/en active IP Right Grant
- 2004-02-12 BR BRPI0406465A patent/BRPI0406465B1/en not_active IP Right Cessation
- 2004-02-12 PL PL376620A patent/PL218548B1/en unknown
- 2004-02-12 DE DE602004031326T patent/DE602004031326D1/en not_active Expired - Lifetime
- 2004-02-12 CA CA2516186A patent/CA2516186C/en not_active Expired - Fee Related
-
2005
- 2005-06-17 ZA ZA200504957A patent/ZA200504957B/en unknown
- 2005-07-04 IL IL169527A patent/IL169527A/en active IP Right Grant
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1386965A (en) * | 1971-03-29 | 1975-03-12 | Aron Md Samuel J | 4-nitro pyridine -1- oxide derivatives nad compositions containing the same |
| WO2000021934A1 (en) * | 1998-10-15 | 2000-04-20 | Astrazeneca Ab | Compounds |
| CN1370047A (en) * | 1999-08-18 | 2002-09-18 | 阿方蒂农科有限公司 | Fungicides |
| CN1390204A (en) * | 1999-08-20 | 2003-01-08 | 道农业科学公司 | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2360627T3 (en) | 2011-06-07 |
| DE602004031326D1 (en) | 2011-03-24 |
| PL218548B1 (en) | 2014-12-31 |
| KR20050101558A (en) | 2005-10-24 |
| US20060052366A1 (en) | 2006-03-09 |
| KR101084022B1 (en) | 2011-11-16 |
| CA2516186A1 (en) | 2004-09-02 |
| BRPI0406465A (en) | 2005-12-06 |
| ATE497957T1 (en) | 2011-02-15 |
| JP2006517948A (en) | 2006-08-03 |
| EP1597252B1 (en) | 2011-02-09 |
| IL169527A (en) | 2011-12-29 |
| PL376620A1 (en) | 2006-01-09 |
| BRPI0406465B1 (en) | 2016-12-27 |
| WO2004074280A1 (en) | 2004-09-02 |
| JP4630271B2 (en) | 2011-02-09 |
| ZA200504957B (en) | 2006-04-26 |
| CA2516186C (en) | 2012-07-31 |
| CN1751039A (en) | 2006-03-22 |
| MXPA05008705A (en) | 2005-10-05 |
| EP1449841A1 (en) | 2004-08-25 |
| EP1597252A1 (en) | 2005-11-23 |
| US7754741B2 (en) | 2010-07-13 |
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